Top Suppliers:I want be here
  • DC Chemicals Limited
  • China
  • Product Name: Isosilybin
  • Price: $650.0/100mg $1100.0/250mg $2200.0/1g
  • Purity: 98.0%
  • Stocking Period: 3 Day
  • Contact: Tony Cao
Related CAS#:
72581-71-6 142796-22-3
142796-21-2

72581-71-6

72581-71-6 structure
72581-71-6 structure
  • Name: Isosilybin
  • Chemical Name: isosilybin
  • CAS Number: 72581-71-6
  • Molecular Formula: C25H22O10
  • Molecular Weight: 482.436
  • Catalog: Biochemical Chinese herbal medicine ingredients
  • Create Date: 2018-06-23 13:37:38
  • Modify Date: 2024-01-02 13:15:16
  • Isosilybin (Isosilybinin) is a flavonoid from milk thistle; inhibits CYP3A4 induction with an IC50 of 74 μM.
Name isosilybin
Synonyms (2R,3R)-3,5,7-Trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-
Isosilybin
isosilibinin
4H-1-Benzopyran-4-one, 2-[2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
3,5,7-Trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2-[2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-
Description Isosilybin (Isosilybinin) is a flavonoid from milk thistle; inhibits CYP3A4 induction with an IC50 of 74 μM.
Related Catalog
Target

IC50: 74 μM (CYP3A4)[1]
In Vitro The reporter gene assay shows that milk thistle’s components silybin and isosilybin are responsible for the inhibition of PXR-mediated CYP3A4 induction by milk thistle. Compared with silybin, its isomer isosilybin is a stronger inhibitor of PXR-mediated CYP3A4 induction. A solution of 89, 133, and 200 μM isosilybin significantly inhibits CYP3A4 induction by 64, 82, and 88%, respectively. Isosilybin inhibits CYP3A4 induction with an IC50 of 74 μM[1]. Isosilybin B and isosilybin A, two diastereoisomers isolated from silymarin, have anti-prostate cancer (PCA) activity that is mediated via cell cycle arrest and apoptosis induction. Isosilybin B and isosilybin A treatment results in growth inhibition and cell death together with a strong G(1) arrest and apoptosis in human prostate cancer LNCaP and 22Rv1 cells[2]. Isosilybin B causes increased phosphorylation of Akt (Ser-473 and Thr-308) and Mdm2 (Ser-166), which is linked with androgen receptor degradation as pretreatment with PI3K inhibitor (LY294002)-restored androgen receptor level. Isosilybin B treatment enhances the formation of complex between Akt, Mdm2 and AR, which promotes phosphorylation-dependent AR ubiquitination and its degradation by proteasome[3]. Isosilybin A is able to significantly activate PPARγ at a concentration of 30 μM (2.08±0.48 fold, p<0.01). Isosilybin A causes transactivation of a PPARγ-dependent luciferase reporter in a concentration-dependent manner. In silico docking studies suggests a binding mode for 3 distinct from that of the inactive silymarin constituents, with one additional hydrogen bond to Ser342 in the entrance region of the ligand-binding domain of the receptor[4].
Cell Assay LNCaP cells and 22Rv1 cells are plated and treated at 40–50% confluency with different doses of isosilybin B and isosilybin A (10–90 μM in medium) dissolved originally in Dimethyl sulfoxide (DMSO) for the desired time periods (24–48 h) in serum condition. An equal amount of DMSO (vehicle) is present in each treatment, including control; DMSO concentration did not exceed 0.1% (v/v) in any treatment. At the end of desired treatments, total cell number is determined by counting each sample in duplicate using a hemocytometer under an inverted microscope. Cell viability is determined using trypan blue exclusion method[2].
References

[1]. Mooiman KD, et al. Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction. Drug Metab Dispos. 2013 Aug;41(8):1494-504.

[2]. Deep G, et al. Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells. Carcinogenesis. 2007 Jul;28(7):1533-42.

[3]. Deep G, et al. Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway. Oncogene. 2008 Jun 26;27(28):3986-98.

[4]. Pferschy-Wenzig EM, et al. Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma. J Nat Prod. 2014 Apr 25;77(4):842-7.
Density 1.5±0.1 g/cm3
Boiling Point 793.0±60.0 °C at 760 mmHg
Molecular Formula C25H22O10
Molecular Weight 482.436
Flash Point 274.5±26.4 °C
Exact Mass 482.121307
PSA 155.14000
LogP 2.59
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.684

Chemsrc provides CAS#:72581-71-6 MSDS, density, melting point, boiling point, structure, formula, molecular weight, synthetic route, etc.
title: CAS No. 72581-71-6 | Chemsrc address: https://m.chemsrc.com/en/baike/600751.html

Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved